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Interaction of Trans-Retinol and 1,1-Diamino-2,2-Dinitroethylene (FOX-7)-A DFT Treatment

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Interaction of Trans-Retinol and 1,1-Diamino-2,2-Dinitroethylene (FOX-7)-A DFT Treatment To Chemistry Journal Vol 3 (2019) ISSN: 2581-7507 http://purkh.com/index.php/tochem Interaction of Trans-Retinol And 1,1-Diamino-2,2-Dinitroethylene (FOX-7)-A DFT Treatment Lemi Türker Middle East Technical University, Department of Chemistry Üniversiteler, Eskişehir Yolu No:1, 06800 Çankaya/Ankara, TURKEY [email protected], [email protected] Abstract: trans-Retinol is a highly conjugated molecule whose oxidized form trans-retinal has prime importance in the metabolism of vision. On the other hand, 1,1-diamino-2,2-dinitroethylene (FOX-7) is a pull-push type insensitive explosive material. The present study considers the interaction between trans-retinol and FOX-7 molecules at the level of B3LYP/6-31+G(d). Some structural, quantum chemical and spectral properties are obtained for the trans-retinol and FOX-7 composite. The calculations indicate that the mode of interaction in the composites of trans-retinol and FOX-7 in one hand and trans-retinal and FOX-7, on the other hand, is different. In the case of trans-retinol, possibly some orbital interactions happen with FOX-7 additionally. Keywords: Retinol, Vitamin A, FOX-7, DADNE, Explosive, DFT. 1. Introduction Retinol (Vitamin A) is a fat-soluble vitamin that belongs to a family of similarly shaped molecules, the retinoids, and occurs in several chemical forms, notably an aldehyde (retinal), alcohol (retinol), and an acid (retinoic acid). In foods of animal origin, the major form of vitamin A is an ester, primarily retinyl palmitate, which is converted to retinol. Precursors to the vitamin (provitamins) are present in foods of plant origin as some of the members of the carotenoid family of compounds [1]. It is readily available from a diversity of both plant and animal matter. Vitamin A is an essential human nutrient for normal metabolic functioning in both the embryo and the adult, including normal cell growth and development and vision [2]. In the metabolism of vision all-trans-retinol is converted to 11-cis-retinol[2]. Vitamin A actually refers to a family of similarly shaped molecules: The retinoids. The basic structure of the retinoid molecule consist of a cyclic end group, a polyene side chain, and a polar end group. The conjugated system formed by alternating C=C double bonds in the polyene side chain is responsible for the color of retinoids (typically yellow, orange, or red). Hence, many retinoids are chromophores. Alternation of side chains and end groups creates the various classes of retinoids [2]. The important part of vitamin A is the retinyl group, which can be found in several forms. CH3 CH3 H3C CH3 OH trans-Retinol CH3 The discovery of vitamin A stemmed from research dating back to 1906, indicating that factors other than carbohydrates, proteins, and fats were necessary to keep cattle healthy [3]. By 1917, one of these substances was independently discovered by Elmer McCollum at the University of Wisconsin-Madison, and Lafayette Mendel and Thomas Osborne at Yale University. Since "water-soluble factor B" (Vitamin B) had recently been discovered, the researchers chose the name "fat-soluble factor A" (vitamin A) [3]. Vitamin A was first synthesized, in 1947, by two Dutch chemists, David Adriaan van Dorp, and Jozef Ferdinand Arens. 85 To Chemistry Journal Vol 3 (2019) ISSN: 2581-7507 http://purkh.com/index.php/tochem FOX-7 (1,1-diamino-2,2-dinitroethylene, diaminodinitroethylene, DADNE) was synthesized in 1998 by researchers of the Swedish Defense Research Agency (FOI) [4,5]. Since then, its explosive potential has been thoroughly investigated [6-20]. FOX-7 is a novel high-energy insensitive material which possesses good thermal stability and low sensitivity. It exhibits excellent application performance among the known insensitive ammunitions and solid propellants. FOX-7, although its structure and molecular composition are simple, exhibits abundant and surprising chemical reactivity (including coordination reactions, nucleophilic substitutions, electrophilic addition reactions, acetylate reactions, oxidizing and reduction reactions, etc., [21,22]). It is due to the presence of amino and nitro groups in its structure. 2. Method of Calculations Initially, MM2 method was employed for the structure optimizations leading to energy minima. Then, semi- empirical PM3 self-consistent fields molecular orbital (SCF MO) method [23,24] at the restricted level [25,26] was used. Subsequent optimizations were achieved at Hartree-Fock level by using various basis sets. Then, the optimizations were managed within the framework of density functional theory (DFT) using B3LYP functional [27,28] at the level of B3LYP/6-31+G(d). The exchange term of B3LYP consists of hybrid Hartree–Fock and local spin density (LSD) exchange functions with Becke’s gradient correlation to LSD exchange [28,29]. The correlation term of B3LYP consists of the Vosko, Wilk, Nusair (VWN3) local correlation functional [30] and Lee, Yang, Parr (LYP) correlation correction functional [31]. Also, the vibrational analyses were done at the same level of calculations employed for the optimizations. The total electronic energies (E) are corrected for the zero point vibrational energy (ZPE) to yield Ec values. The normal mode analysis for each structure yielded no imaginary frequencies for the 3N−6 vibrational degrees of freedom, where N is the number of atoms in the system. This indicates that the structure of each molecule corresponds to at least a local minimum on the potential energy surface. All these calculations were done by using the Spartan 06 package program [32]. 3. Results and Discussion FOX-7 molecule has electron donor amino groups and electron acceptor nitro groups oriented in such a way that a pull-push type system arises. It has a dipole moment of 8.66 D (calc.). On the other hand, trans-retinol possesses an endocyclic double bond but four trans double bonds constituting highly conjugated molecular system. The three methyl groups along the conjugated path are inductively electron donors. Note that endocyclic double bond may also be in conjugation with the unsaturated side moiety. When FOX-7 and trans-retinol systems are in the vicinity of each other, main factors of interaction might be charge-charge, dipole-dipole, charge-dipole even the orbital interactions. Figure 1 shows the systems considered presently. The notation, trans-retinol+FOX-7, stands for the composite system of trans-retinol and FOX-7. The figure also displays the direction of the dipole moment vectors. In the composite, the positive tail of the dipole moment vector resides on the retinol moiety, and the head aims at FOX-7. Thus, indicating the donor and acceptor components. FOX-7 86 To Chemistry Journal Vol 3 (2019) ISSN: 2581-7507 http://purkh.com/index.php/tochem trans-Retinol trans-Retinol+FOX-7 Figure 1. Optimized structures of the chemical systems considered (from different angles of view). As seen in the figure, the NO2 groups of FOX-7 molecule prefer to orient themselves nearby the carbinol part of the retinol system. Possibly, a hydrogen bonding forms. The shortest distance between O-H and NO2 oxygen is 2.078 Å. Figure 2 shows the calculated bond lengths of the optimized structures considered. The bond lengths of the composite system (trans-retinol+FOX-7) are different from the respective bond lengths of each component. Figure 3 shows the charges (ESP) on the atoms of the species considered (Hydrogens not shown). Note that ESP charges are obtained by the program based on a numerical method that generates charges that reproduce the electrostatic field from the entire wave function [32]. As seen in Figure 3, the charges on the respective atoms of each component are different from they are in the composite. Figure 4 shows the calculated IR spectra of the systems considered. As seen in the figure, the spectrum of the composite differs from the spectrums of the components in terms of positions and intensities of the peaks as well as some missing and additional peaks. FOX-7 87 To Chemistry Journal Vol 3 (2019) ISSN: 2581-7507 http://purkh.com/index.php/tochem trans-Retinol trans-Retinol +FOX Figure 2. Calculated bond lengths of the optimized structures considered (Hydrogens not shown). FOX-7 trans-Retinol 88 To Chemistry Journal Vol 3 (2019) ISSN: 2581-7507 http://purkh.com/index.php/tochem trans-Retinol+FOX-7 Figure 3. ESP charges on the atoms of the spcies considered (Hydrogens not shown). FOX-7 trans-Retinol trans-Retinol+FOX-7 Figure 4. Calculated IR spectra of the species considered. 89 To Chemistry Journal Vol 3 (2019) ISSN: 2581-7507 http://purkh.com/index.php/tochem Table 1 shows various energies of the systems considered where E, ZPE, and Ec stand for the total electronic energy, zero point vibrational energy and ZPE corrected total electronic energy, respectively. Table 1.Various energies of the systems considered. System E ZPE Ec FOX-7 -1570947.81 241.57 -1570706.24 trans-Retinol -2245823.53 1191.68 -2244631.85 trans-Retinol+FOX-7 -3816795.88 1438.46 -3815357.42 Energies in kJ/mol. Note that the sum of Ec values of FOX-7 and trans-retinol is -3815338.08 kJ/mol., whereas the respective value of the composite is -3815357.42 kJ/mol., which indicates that some stabilization exists in forming the composite system. On the other hand, using the information included in Table 2, ΔG˚reac for the composite formation is +47.95528 kJ/mol. Thermodynamically the composite formation is not favorable (at the standard conditions) which might be due to the unfavorable entropy change (-237 J/mol) accompanying the composite formation. System Hº (kJ/mol.) Sº (J/molº) Gº (kJ/mol.) FOX-7 -1570696.349 373.83 -1570807.808 trans-Retinol -2244597.167 589.24 -2244772.851 trans-Retinol+FOX-7 -3815316.229 726.07 -3815532.703 Figure 5 displays the UV-VIS spectra (time-dependent DFT) of the systems considered.
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